Ethyl Acetate → ethyl 1-isobutyl-5-methyl-1H-indole-2-carboxylate

HRID 2249692Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH:23]([CH3:25])[CH3:24].C(OCC)(=O)C>CN(C)C=O.O>[CH2:22]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:23]([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 120 °C

Procedure

In 30 ml of N,N-dimethylformamide are suspended 2.81 g of ethyl 5-methyl-1H-indole-2-carboxylate, 17.0 g of potassium carbonate and 11.3 ml of isobutyl iodide. The suspension is stirred at 120° C. for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent: toluene) to obtain 1.75 g of ethyl 1-isobutyl-5-methyl-1H-indole-2-carboxylate as a light yellow oily product.

Workup

customthe organic layer is separated
customThe organic layer thus obtained
washis washed with water and saturated aqueous solution of sodium chloride successively
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure
customThe residue thus obtained
customis purified by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record: ord-63b7e3dc8dd64dea90af975b141d5d1b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314888B1

Reaction notes

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